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13C NMR spectral characterization of epimeric rotenone and some related tetrahydrobenzopyranofurobenzopyranones

Journal of Heterocyclic Chemistry

None
By:
and
DOI: 10.1002/jhet.5570200649

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Abstract

The 13C nuclear magnetic resonance (nmr) spectra of epimers of rotenone and four 12a-hydroxy-analogues were examined to determine the stereochemical effect of the B/C ring fusion involving the 6a- and 12a-carbon centers. Chemical shift differences between the epimeric carbon resonances of cis- and trans-6a,12a-compounds were notably larger than those of diastereoisomers derived from the same B/C ring junction stereochemistry. Results of the spectral analysis have been useful for the quantification of mixtures of epimers and for the measurement of rates of epimerization and oxygenation.

Additional Publication Details

Publication type:
Article
Publication Subtype:
Journal Article
Title:
13C NMR spectral characterization of epimeric rotenone and some related tetrahydrobenzopyranofurobenzopyranones
Series title:
Journal of Heterocyclic Chemistry
DOI:
10.1002/jhet.5570200649
Volume
20
Issue:
6
Year Published:
1983
Language:
English
Publisher:
Wiley
Publisher location:
Hoboken, NJ
Contributing office(s):
Upper Midwest Environmental Sciences Center
Description:
6 p.
Larger Work Type:
Article
Larger Work Subtype:
Journal Article
Larger Work Title:
Journal of Heterocyclic Chemistry
First page:
1687
Last page:
1692
Number of Pages:
6